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2,125 Siesta Key Holiday Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Siesta Key holiday rentals from 10 rental sites including HomeAway, Booking.com, TripAdvisor and more, from $25 a night.

Siesta Key Information

About Siesta Key

Siesta Key is a small barrier island off the coast of Florida with the Gulf of Mexico on the west and Roberts Bay to the east. Only about 3.5 square miles, Siesta Key has a relaxed, suburban atmosphere that draws tourists and locals who want to get away from it all, but still have easy access to mainland amenities.

Things to do in Siesta Key

Siesta Key is best known for its warm, clear beaches. Siesta Key Public Beach, voted the 3rd Best Beach in the US by TripAdvisor users, is the most popular on the island. While this long-time favorite and nearby Crescent Beach are known for their soft, spotless sand, Turtle Beach is hailed as the perfect place for collecting shells. Surfing, volleyball, scuba diving, fishing, boating, jet skiing, and even parasailing are all beach activities available at one or more beaches on Siesta Key. Downtown hosts a wealth of dining and shopping options from family-friendly restaurants to a host of clubs and nightlife spots. Explore the island’s natural beauty with a hike, bike ride, or walk to the Point of Rocks to spot rare marine life and birds.

Siesta Key Accommodations

Even though it is an island, Siesta Key is not difficult to reach. Fly into the Sarasota-Bradenton International Airport, just 8 miles from the center of Siesta Key, and drive into town via one of the two drawbridges that connect it to the mainland. If you want to get started on your vacation right away, you can even take a ferry or boat from nearby Sarasota. Finding a vacation rental with a view or pool within your price range will not be a challenge with Tripping’s wide variety of properties available on Siesta Key!

Vacation Rentals in Siesta Key

Find the best Siesta Key vacation rentals on Tripping.com. With over 2125 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Siesta Key range from $25 a night. Many rentals can also be booked directly online.

Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 1982 homes in Siesta Key offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 1468 rentals with pool or jacuzzi, or relax with the family in one of the 1837 homes with cable TV.

For all those pet owners with dogs or cats, Siesta Key offers 327 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com.

Search properties from 10 vacation rental sites in Siesta Key where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 1232 HomeAway rentals, 316 Booking.com short term rentals and 310 TripAdvisor vacation rentals.